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Organic reaction mechanisms 40 solved cases
  • 作 者:Mar Gómez Gallego ; M. A. Sierra
  • 出 版 社:Springer
  • 出版年份:2004
  • ISBN:3540003525
  • 标注页数:292 页
  • PDF页数:301 页
  • 请阅读订购服务说明与试读!

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Level 1 1

Case 1. A Surprise in the Synthesis of Guanacastepene A 1

Case 2. Sulfenylation of Indole 7

Case 3. Substrate Selective Reactions in the Presence of Lewis Acids 13

Case 4. Diastereoselective Reductions of β-Ketoesters 21

Case 5. Rearrangements from Tetrahydropyran Derivatives 27

Case 6. Stereospecific Substitution Reactions of Epoxy Sulfides 33

Case 7. NaBH4 Reduction of α,β-Unsaturated Chromium Carbene Complexes 39

Case 8. Addition of Hydroxylamines to α,β-Unsaturated Esters 47

Case 9. Solvolysis of Electron-Deficient Norbomyl Triflates 55

Case 10 Nucleophile Versus Base Catalysis 63

Case 11. The Hydrolysis ofp-Substituted Styrene Oxides 69

Case 12. Elimination Reactions of Benzaldehyde O-Benzoyloximes 79

Case 13. Oxygen Versus Sulfur Stabilization of Carbenium Ions 87

Case 14. Cyclization of 2,3-Dibenzylidenesuccinates 97

Case 15. Oxazoline N-Oxides as Dipoles in [3+2] Cycloadditions 101

Case 16. Light-Induced Cycloadditions of N-Phthaloyl α-Amino Acids 107

Level 2 113

Case 17. Change in Rate-Determining Step in an E 1 cB Mechanism:Aminolysis of Sulfamate Esters 113

Case 18. Unusual Diels-Alder Reactivity of Acyclic 2-Azadienes 119

Case 19. Chelate-Controlled Carbonyl Addition Reactions 125

Case 20. Esterification of Carboxylic Acids with Dimethyl Carbonate and DBU 131

Case 21. A Hammett Analysis in a Multistep Reaction:Rhodium(Ⅱ)-Catalyzed Decomposition of α-Diazo Esters 139

Case 22. Tandem Cycloadditions with Nitronates 145

Case 23. Hydrolysis of 2-Aminobenzoate Esters 153

Case 24. Rearrangements of Cyclobutenones 159

Case 25. Epoxi Ester-Orthoester Rearrangement 163

Case 26. 2-Chloro-1,3,5-triazines as Activating Groups of Carboxylic Acids in the Formation of Peptide Bonds 169

Case 27. Acid-Catalyzed Isomerization of Imines 177

Case 28. A Dearomatizing Disrotatory Electrocyclic Ring Closure 183

Case 29. Stereoselective Debromination of Vicinal Dibromides 189

Case 30. Diels-Alder Reactions of N-Acyl-1,2,4,5-tetrazines 197

Case 31. Stereoselective Synthesis of 2-Acylaziridines 203

Level 3 211

Case 32. The Baylis-Hillman Reaction 211

Case 33. The Rate-Determining Step in the SNAr Reaction 217

Case 34. Helicenophanes and their Racemization 225

Case 35. Solvolysis of Vinyl Iodonium Salts 231

Case 36. Vicarious Nucleophilic Substitution 237

Case 37. Base-promoted HF Elimination from 4-Fluoro-4-(4′-nitrophenyl)butan-2-one 243

Case 38. Substitution of β-Halostyrenes by MeS- 251

Case 39. Periodinane-Mediated Cyclization of Anilides 259

Case 40. Solvolysis of 8-Deltacyclyl Brosylates 269

Subject Index 277

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